Hydrochloric Acid → HCID 13729867, compound

HRID 413504Notes

Reaction equation

[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].[C:17](OC)(=[O:22])[C:18]([O:20][CH3:21])=[O:19].Cl>O1CCCC1>[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:17](=[O:22])[C:18]([O:20][CH3:21])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of the Grignard reagent prepared from E-1-phenyl-2-(2-bromophenyl)ethylene (8.56 g) and magnesium (0.96 g) in dry tetrahydrofuran (20 ml) was added dropwise over 30 minutes to a stirred solution of dimethyl oxalate (7.76 g) in dry tetrahydrofuran (70 ml) cooled to −15° C. The resulting mixture was stirred at about −15° C. for 30 minutes, then at room temperature for 1 hour, then poured into dilute hydrochloric acid and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as a yellow oil (17.22 g). Purification by column chromatography using dichloromethane and petrol (1:1) as eluant then evaporative distillation (0.07 torr, oven temperature 170° C.) gave E-methyl 2-(2′-phenylethenyl)phenylglyoxalate (2.01 g, 23% yield) as a yellow oil, pure by GC, 1H nmr (CDCl3): delta 3.78 (3H, s), 6.88 (centre of 2 doublets, each 1H, J 16 Hz) p.p.m.

Workup

waitat room temperature for 1 hour
extractionextracted with ether
washThe extracts were washed with water
customdried
concentrationconcentrated
customto give the crude product as a yellow oil (17.22 g)
customPurification by column chromatography
distillationdistillation (0.07 torr, oven temperature 170° C.)

Sources & evidence

ORD record: ord-14854ee7459344c8bdacfadf821ce524
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566547B1

Reaction notes

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